An honest conversation on the evolution of Taylor Swift

Two Taylor Swift observers, and occasional sympathizers, speak candidly on 13 years of the country-pop czarina, from her self-titled debut to Lover.

June 21, 2019
An honest conversation on the evolution of Taylor Swift Peter Kramer/Frazer Harrison/Larry Busacca/Jamie McCarthy/Jason Merritt/Kevin Winter/Getty Images / Illustration by The FADER

It’s been thirteen years since Taylor Swift unleashed her debut single, “Tim McGraw.” She was blond curly-haired blue-eyed, singing with a slight country twang about boys in Chevy trucks, faded blue jeans, and dancing outside at midnight, and the world loved her.


Flash-forward to the present, Swift has reigned the pop charts for nearly every album that followed her debut, though it was an ascent that wasn’t without controversy, and a social climate that, with the wind of every new album cycle, ran amok with opinions.

Now, in the midst of her seventh album cycle for Lover, Swift seems to be catering to a portion of her fanbase that feels unaligned with those that have grown up with her music since middle school. As two Swift observers and occasional sympathizers, it’s been bizarre for us to understand where exactly she’s going with her new record. Packaged as a glitter and rainbow Pride themed-project that feels more distanced than ever from the intimate songcraft of her earlier work, Lover has, so far, left us underwhelmed in several regards.


In an effort to try and understand how Swift’s gotten to where she is now, we looked back upon her near decade-and-a-half body of work, and we discovered for better or for worse, Swift has rarely strayed too far from the position in which she emerged, thirteen years ago.

Taylor Swift (2006)


SALVATORE MAICKI: So, when Taylor Swift’s self-titled album came out, I believe it was 2006. What was your first reaction to who this girl was?

STEFFANEE WANG: I was in middle school. All I remember from this was “Teardrops From My Guitar" and “Our Song,” which I really loved. I ripped her videos from YouTube and saved them on my iTunes. I don’t even remember if I had any opinions on this album — I feel like I just kinda consumed it and I was like this is on the radio and I’m going to listen to it.


MAICKI: I was initially turned off because she reminded someone who would not be friends with me in middle school, emphasized by the fact that she used gay as an insult in “Picture To Burn.” It was a different time, sure, but it was harder for me to relate. She reminded me of someone whose parents have informed all of their politics, which I guess makes sense considering she made the album when she was a child.

WANG: Everything about this album imagery-wise was very innocent, in the way a tween movie would be. I mean she's singing about sneaking out with her boyfriend, riding around with her boyfriend, etc. etc. etc. Tame and parent-friendly topics that I'm sure boosted her CD-sales at the time.

MAICKI: This album might be Taylor's strongest embodiment of traditional Nashville "Music Row" energy. Each release from here forward makes it more obvious she's actually from suburban Pennsylvania.

Fearless (2008)

MAICKI: I didn’t fuck with Taylor Swift until Fearless, which came out two years later, in 2008. It was her real breakout, an establishment of Taylor Swift-ness, in the most traditional sense. You couldn’t go anywhere without hearing those songs.

WANG: Her first two albums felt so seamless and cohesive, like a natural kind of progression, rather than a separate era. She was definitely leaning into the traditional. The “Love Story” music video is essentially a Romeo and Juliet remake. It's very picturesque, very fairytale-ish. She was 18 at the time, but the concept made sense for her because she was still a teenager. She felt very relatable, and as a result her songs felt very real. I feel like this was her most untroubled era.

MAICKI: Definitely, and I would be pressed to criticize anything about it either. There's nothing edgy about this album, but I was here for it then and I'm still here for it now.

Speak Now (2010)

MAICKI: This just feels like an extension of Fearless, the album embodiment of “if it ain’t broke, don’t fix it.” Aesthetically it doubled down on the childlike fairy tale thing, which felt slightly more juvenile the second time around. We do get to hear about how John Mayer fucked her over, and “The Story of Us” is genuinely one of the best Taylor Swift songs of all time. But I can’t get over how corny that album cover is. What is with that gold text? It lacked any kind of mature concept beyond “I’m a princess.”

WANG: The concept was just so traditional again, leaning into dated. Still, this was a CD cover that your mom would let you buy at Target. But... I liked some of the songs: "Speak Now," "Enchanted," "If This Was A Movie"! She's always been good at writing personal songs that you knew are corny but still hit your heart. I agree though, it was boarding on juvenile.

MAICKI: For her third album, it’s too safe. But safety has always been a core Taylor Swift value.

WANG: Sadly, maybe these are just her tastes, and this is what she thinks looks good.

MAICKI: Yeah I think this is where you first start to get the idea that Taylor Swift has bad taste.

WANG: Do you think like this could be her trying to keep it safe for how young her fanbase is? Her fanbase has always been really young. She was kinda like a Disney star without being from Disney. Even though she’s like six years older than us, young kids would still be listening to her music and I think she was very conscious of that.

Red (2012)

MAICKI: My take is that Taylor has only made one major aesthetic pivot in her career, and it was Red. Everything else has been a stylistic variation on Red. She’s kept the bangs ever since. To me, this was the perfect intersection between stadium pop and her country roots.

WANG: How old is she here, like 22? For me, this was kinda the moment when Taylor Swift presents herself as growing up. She decided she didn’t want to be twirling in dresses anymore, at least not on her album covers anymore, and was like I’m moving into pop. I’m not as wholesome or pandering to my audience’s parents anymore. She has the bold red lipstick and the short shorts. It still feels very precious, but at that point that's just her brand.

MAICKI: That era was more aesthetically aligned with the times than anything she’s ever put out. Look at the Piknik-esque cross process filter on these promo pics. I'm still kind of here for it, as a product of 2012.

WANG: I look at it now as dated, but I remember it was so trendy and cool. I'm pretty sure I went out and bought red lipstick around this time and I used those movie theater black frame 3D glasses as a poor substitution for the ones she wears in the "22" music video. So many people at my high school dressed like her for Halloween in this era. Everything considered, her presentation here didn’t feel performative.

MAICKI: The songs on this album feel undoubtably timeless, so long as we're excluding the bass drop in "I Knew You Were Trouble." Red was a genuine landmark moment for her, and one I'm always ready to revisit.

1989 (2014)

MAICKI: So 1989 was the big chop. I love 1989, I’ll preface it with that. This is the first time Taylor really acknowledged the public’s perception of her, and it felt — at least at first — extremely self aware. She had a sense of humor about herself, and people were excited about it.

WANG: I think her writing on this album is really clever. I think a lot about that line "I was nightmare dressed like a daydream" from "Blank Space." It brought the Taylor Swift we knew she could be.

MAICKI: Her stylistic choices for this album started off so on point, with the Polaroids and the Tumblr-bred eighties nostalgia. Even though it was the biggest album on the planet, something felt remarkably intimate about it. But this also marked the beginning of a strange regression, in that once the album bloated past a certain point, it got kind of messy. The entire “Bad Blood” rollout — attempting to annihilate Katy Perry with action movie CGI and an out-of-place Kendrick Lamar feature — was petulant and aesthetically oversaturated. And “Wildest Dreams,” one of the best tracks of the record, was soiled by its own video.

WANG: Yeah, I remember the video with its glamorization of British colonial-era style and setting, while there simultaneously being no black people in the video. That brand of bygone-era nostalgia always comes off as weird and irresponsible. I’m sure she had innocent intentions — but these mistakes came off as so tone-deaf for their time. She was 24, and it felt like this was an issue that could've been easily prevented if she were a little bit more attentive to the cultural climate. Whatever past innocence or wholesomeness she embodied that caused people to overlook her past errors weren’t convincing people anymore. Then, she started building that victim-narrative with all the celebrity beefs she was getting herself into.

MAICKI: It felt like a switch flipped about midway through the album cycle — sometime in 2015 — where she was too huge. Maybe she felt like she could get away with anything, because this is when these real goofy creative decisions started manifesting. You have the biggest album in the world, so why are you dressing like that?

Reputation (2017)

WANG: Was this the first time there was outrage over album art simply because it was…ugly? It was like the “graphic design is my passion” meme, and was like, where did Taylor Swift’s money go? I feel like this could be a running theme for most of the imagery throughout all her eras, actually. I sometimes wonder if she presents herself as intentionally naïve when she comes up with album and music video concepts. Also, why couldn’t she at least have used real text from real articles instead of just her name for all the copy?

MAICKI: It felt like something that would’ve been nominated for a Nickelodeon Kids Choice Award in 2004, and I mean that in a bad way. Everything about this era was aesthetically atrocious, from the fonts to the styling to the music videos. And that’s a shame, because there were some real jams on that album. I'm looking at you, "Getaway Car."

WANG: Why did Taylor Swift’s edgy version of a bad girl still look so... wholesome? I mean the entire “Look What You Made Me Do” video, with her dressing up as all her past alter-egos and declaring the "old Taylor is dead" is so... villain from a children’s movie. And that extended into her writing too. I think that’s why her “edgier” songs addressing her reputation and her feuds didn’t work for me because some of the issues that she was getting pushback for weren’t childish issues. So the concept as a whole kinda fall flat, and made it disingenuous and corny.

MAICKI: People wrote this album off immediately, and part of that definitely had to do with the bad singles and her public image coming out of 1989. But I can’t help but feel like a lot of it had to do with the literal imagery. Nobody asked for that CGI snake.

WANG: It sucks because there are some really great songs on the record! “Delicate” is probably one of my favorite songs of hers, ever. “Endgame” slaps, don't @ me. The video for "Endgame" is surprisingly one of her better ones, visually, because it’s just her looking rich and hanging out with rich people on a yacht. There's no posturing. For “Delicate” she does her awkward/weird act in the form of a Maddie Ziegler-interpretive dance which comes off really hammy — she’s literally the embodiment of European beauty standards. That video does not do that song justice.

MAICKI: More than anything, this album crystallized that, although Taylor makes good music, her taste can skew mad corny.

Lover (2019)

WANG: Can I start by saying that everything about the visuals this album cycle has made me cringe. I’m sorry, but if I was a thirty year old, I don’t think I would be dressing like this. I think Kacey Musgraves is a great counter example because she does the glitter and sequins but there’s an obvious note of camp in her presentation, coupled with the earnesty in her music... it works really well. But Taylor…even the image of the snake bursting into butterflies, which has shown up twice now, is so on the nose; and yet the optimism she’s trying to sell me isn’t landing.

MAICKI: I think there is a way you can dress colorful and optimistic without looking like an Easter egg. Look, obviously I have my gripes with Taylor Swift, but I’m also rooting for her to grow up and deliver a mature, refined body of work. I know she has it in her, but I just feel in my gut that it's not gonna be Lover, judging from the eighteen-song tracklist (editing and the egregious lens flares on all the promotional photos. Like, is that a fucking unicorn earring, Taylor?

WANG: It reminds me of the photos I would reblog in 2010 on Tumblr of like, Strawberries & Crème frappuccinos next to a pile of glitter. Which is a fine thing to like! It’s just strange now to see someone build a whole concept around that now in the year 2019. Especially from a 29-year-old.

MAICKI: I will say that I enjoy “You Need To Calm Down,” even if I definitely don't subscribe to the brand of gayness it attempts to market. The hook slaps, and I don’t think the video is quite as harmful as many people are making it out to be. I just wish she hired more tasteful gays to execute whatever her vision was.

WANG: Yeah — the style choices felt more deliberate, and fitting. It’s corny, but forgivably. It’s still saturated with privilege and money and a weird, out-of-the-blue Katy and Tay reunion, but...were we expecting something actually, truly radical from Swift? One thing I am still puzzled by is if the entire album is going to keep the “pride” rainbow styling. That seems weird and potentially bad. Her surprise appearance at the Stonewall Inn this past weekend didn't help and felt exploitative, if not at least completely unnecessary.

MAICKI: Expecting radical from Taylor would be short-sighted, at this point. Keep in mind how her fanbase extends out far beyond enlightened political analyses of her work — many of them probably live in rural places where it’s still not okay to be openly gay, and I truly I think it all boils down to the fact that we’re not Taylor’s targeted audience anymore, which is strange considering we grew up with her music.

WANG: This is true. But I also want to demand more from her visually and creatively — I want to be her targeted audience again. It’s easy for a huge artist like herself to become stagnant, sitting on her unreachable throne of comfort. Clearly, she’s losing impact — “ME!” didn’t go #1 on the charts. I think she needs another Red reinvention moment.

MAICKI: Maybe losing impact could be a good thing? Maybe she needs to break from being infallible, and maybe then, once there’s a few less eyes locked in on every move she makes, she can finally deliver something liberated from the tack of a Target advertisement. I’m not holding my breath, but I want that for her.

An honest conversation on the evolution of Taylor Swift